Anti-glycemic potential of benzophenone thio/semicarbazone derivatives: synthesis, enzyme inhibition and ligand docking studies

References

• Alexacou, K.-M., Tenchiu Deleanu, A.-C., Chrysina, E. D., Charavgi, M.-D., Kostas, I. D., Zographos, S. E., Oikonomakos, N. G., & Leonidas, D. D. (2010). The binding of β-d-glucopyranosyl-thiosemicarbazone derivatives to glycogen phosphorylase: A new class of inhibitors. Bioorganic & Medicinal Chemistry, 18(22), 7911–7922. https://doi.org/10.1016/j.bmc.2010.09.039
   PubMed Web of Science ®Google Scholar
• Arshia, A., Khan, A., Khan, K. M., Saad, S. M., Siddiqui, N. I., Javaid, S., Perveen, S., & Choudhary, M. I. (2016). Synthesis and urease inhibitory activities of benzophenone semicarbazones/thiosemicarbazones. Medicinal Chemistry Research, 25(11), 2666–2679. https://doi.org/10.1007/s00044-016-1673-0
   Web of Science ®Google Scholar
• Arshia, Abbasi, S., Rasheed, S., Khan, J. A., Saad, S. M., Khan, K. M., & Choudhary, M. I. (2020). In vitro antiglycation and antioxidant properties of benzophenone thiosemicarbazones. Pakistan Journal of Pharmaceutical Sciences, 33(3), 1147–1153.
   PubMed Web of Science ®Google Scholar
• Baig, M. M. F. A., Naveed, M., Abbas, M., Chunxia, W., Ullah, S., Hasnat, M., Shad, A., Sohail, M., Khan, G. J., & Ansari, M. T. (2019). DNA scaffold nanoparticles coated with HPMC/EC for oral delivery. International Journal of Pharmaceutics, 562, 321–332. https://doi.org/10.1016/j.ijpharm.2019.03.054
   PubMed Web of Science ®Google Scholar
• Brandt, I., Joossens, J., Chen, X., Maes, M. B., Scharpé, S., De Meester, I., & Lambeir, A. M. (2005). Inhibition of dipeptidyl-peptidase IV catalyzed peptide truncation by vildagliptin ((2S)-{[(3-hydroxyadamantan-1-yl)amino]acetyl}-pyrrolidine-2-carbonitrile). Biochemical Pharmacology, 70(1), 134–143. https://doi.org/10.1016/j.bcp.2005.04.009
   PubMed Web of Science ®Google Scholar
• Caron, J., Domenger, D., Dhulster, P., Ravallec, R., & Cudennec, B. (2017). Using Caco-2 cells as novel identification tool for food-derived DPP-IV inhibitors. Food Research International (Ottawa, Ont.), 92, 113–118. https://doi.org/10.1016/j.foodres.2017.01.002
   PubMed Web of Science ®Google Scholar
• Divar, M., Khalafi-Nezhad, A., Zomorodian, K., Sabet, R., Faghih, Z., Jamali, M., Pournaghz, H., & Khabnadideh, S. (2017). Synthesis of some novel semicarbazone and thiosemicarbazone derivatives of isatin as possible biologically active agents. Journal of Pharmaceutical Research International, 17(6), 1–13. https://doi.org/10.9734/JPRI/2017/35243
   Google Scholar
• Friesner, R. A., Banks, J. L., Murphy, R. B., Halgren, T. A., Klicic, J. J., Mainz, D. T., Repasky, M. P., Knoll, E. H., Shelley, M., Perry, J. K., Shaw, D. E., Francis, P., & Shenkin, P. S. (2004). Glide: A new approach for rapid, accurate docking and scoring. 1. Method and assessment of docking accuracy. Journal of Medicinal Chemistry, 47(7), 1739–1749. https://doi.org/10.1021/jm0306430
   PubMed Web of Science ®Google Scholar
• Friesner, R. A., Murphy, R. B., Repasky, M. P., Frye, L. L., Greenwood, J. R., Halgren, T. A., Sanschagrin, P. C., & Mainz, D. T. (2006). Extra precision glide: Docking and scoring incorporating a model of hydrophobic enclosure for protein–ligand complexes. Journal of Medicinal Chemistry, 49(21), 6177–6196. https://doi.org/10.1021/jm051256o
   PubMed Web of Science ®Google Scholar
• Halgren, T. A., Murphy, R. B., Friesner, R. A., Beard, H. S., Frye, L. L., Pollard, W. T., & Banks, J. L. (2004). Glide: A new approach for rapid, accurate docking and scoring. 2. Enrichment factors in database screening. Journal of Medicinal Chemistry, 47(7), 1750–1759. https://doi.org/10.1021/jm030644s
   PubMed Web of Science ®Google Scholar
• Hsu, C. Y., Sulake, R. S., Huang, P.-K., Shih, H.-Y., Sie, H.-W., Lai, Y.-K., Chen, C., & Weng, C. F. (2015). Synthetic (+)-antroquinonol exhibits dual actions against insulin resistance by triggering AMP kinase and inhibiting dipeptidyl peptidase IV activities. British Journal of Pharmacology, 172(1), 38–49. https://doi.org/10.1111/bph.12828
   PubMed Web of Science ®Google Scholar
• Kalaiarasi, G., Jain, R., Puschman, H., Chandrika, S. P., Preethi, K., & Prabhakaran, R. (2017). New binuclear Ni(II) metallates containing ONS chelators: Synthesis, characterisation, DNA binding, DNA cleavage, protein binding, antioxidant activity, antimicrobial and in vitro cytotoxicity. New Journal of Chemistry, 41(7), 2543–2560. https://doi.org/10.1039/C6NJ03516G
   Web of Science ®Google Scholar
• Kaplancıklı, Z. A., Altıntop, M. D., Sever, B., Cantürk, Z., & Özdemir, A. (2016). Synthesis and in vitro evaluation of new thiosemicarbazone derivatives as potential antimicrobial agents. Journal of Chemistry, 2016, 1–7. https://doi.org/10.1155/2016/1692540
   Web of Science ®Google Scholar
• Kato, E., Kawakami, K., & Kawabata, J. (2018). Macrocarpal C isolated from Eucalyptus globulus inhibits dipeptidyl peptidase 4 in an aggregated form. Journal of Enzyme Inhibition and Medicinal Chemistry, 33(1), 106–109. https://doi.org/10.1080/14756366.2017.1396458
   PubMed Web of Science ®Google Scholar
• Kpomah, B. (2017). Spectroscopic characterization, antimicrobial and toxicological properties of derivatised thiosemicarbazone transition metal complexes. Saudi Journal of Medical and Pharmaceutical Sciences, 2(12), 318–325.
   Google Scholar
• Kulkarni, N. V., Revankar, V. K., Kirasur, B. N., & Hugar, M. H. (2012). Transition metal complexes of thiosemicarbazones with quinoxaline hub: An emphasis on antidiabetic property. Medicinal Chemistry Research, 21(5), 663–671. https://doi.org/10.1007/s00044-011-9576-6
   Web of Science ®Google Scholar
• Nongonierma, A. B., Mooney, C., Shields, D. C., & Fitzgerald, R. J. (2013). Inhibition of dipeptidyl peptidase IV and xanthine oxidase by amino acids and dipeptides. Food Chemistry, 141(1), 644–653. https://doi.org/10.1016/j.foodchem.2013.02.115
   PubMed Web of Science ®Google Scholar
• Prabahar, K., Udhumansha, U., & Qushawy, M. (2020). Optimization of thiolated chitosan nanoparticles for the enhancement of in vivo hypoglycemic efficacy of sitagliptin in streptozotocin-induced diabetic rats. Pharmaceutics, 12(4), 300. https://doi.org/10.3390/pharmaceutics12040300
   Web of Science ®Google Scholar
• Rajak, H., Jain, D. K., Singh, S., Singh, A., K., Patel, V., Veerasamy, R., S., & Pawar, R. (2017). Novel pyrimidine based semicarbazones: Confirmation of four binding site pharmacophoric model hypothesis for antiepileptic activity. Central Nervous System Agents in Medicinal Chemistry, 17(1), 64–71. https://doi.org/10.2174/1871524916666160330122625
   Google Scholar
• Sadir, R., Imberty, A., Baleux, F., & Lortat-Jacob, H. (2004). Heparan sulfate/heparin oligosaccharides protect stromal cell-derived factor-1 (SDF-1)/CXCL12 against proteolysis induced by CD26/dipeptidyl peptidase IV. The Journal of Biological Chemistry, 279(42), 43854–43860. https://doi.org/10.1074/jbc.M405392200
   PubMed Web of Science ®Google Scholar
• Schrodinger. (2019). 1: Schrödinger Suite 2019-1 Protein Preparation Wizard, Epik,. Schrödinger, LLC. 2019. Impact, Schrödinger, LLC, New York.
   Google Scholar
• Schrodinger. (2019a). Schrödinger Release 2019-1: Glide., Schrödinger, LLC.
   Google Scholar
• Schrodinger. (2019b). Schrödinger Release 2019-1: LigPrep., Schrödinger, LLC.
   Google Scholar
• Sever, B., Soybir, H., Görgülü, Ş., Cantürk, Z., & Altıntop, M. D. (2020). Pyrazole incorporated new thiosemicarbazones: Design, synthesis and investigation of DPP-4 inhibitory effects. Molecules, 25(21), 5003. https://doi.org/10.3390/molecules25215003
   Web of Science ®Google Scholar
• Shehzad, M. T., Imran, A., Njateng, G. S. S., Hameed, A., Islam, M., Al-Rashida, M., Uroos, M., Asari, A., Shafiq, Z., & Iqbal, J. (2019). Benzoxazinone-thiosemicarbazones as antidiabetic leads via aldose reductase inhibition: Synthesis, biological screening and molecular docking study. Bioorganic Chemistry, 87, 857–866. https://doi.org/10.1016/j.bioorg.2018.12.006
   PubMed Web of Science ®Google Scholar
• Silva, B. V., & Silva, B. N. M. (2017). Thio- and semicarbazones: Hope in the search for treatment of leishmaniasis and Chagas disease. Medicinal Chemistry (Shariqah (United Arab Emirates)), 13(2), 110–126. https://doi.org/10.2174/1573406412666160909152614
   PubMed Web of Science ®Google Scholar
• Song, J. J., Wang, Q., Du, M., Ji, X. M., & Mao, X. Y. (2017). Identification of dipeptidyl peptidase-IV inhibitory peptides from mare whey protein hydrolysates. Journal of Dairy Science, 100(9), 6885–6894. https://doi.org/10.3168/jds.2016-11828
   PubMed Web of Science ®Google Scholar
• Tanwar, O., Tanwar, L., Shaquiquzzaman, M., Alam, M. M., & Akhter, M. (2014). Structure based virtual screening of MDPI database: Discovery of structurally diverse and novel DPP-IV inhibitors. Bioorganic & Medicinal Chemistry Letters, 24(15), 3447–3451. https://doi.org/10.1016/j.bmcl.2014.05.076
   PubMed Web of Science ®Google Scholar
• Xie, M.-J., Zhu, M.-R., Lu, C.-M., Jin, Y., Gao, L.-H., Li, L., Zhou, J., Li, F.-F., Zhao, Q. H., Liu, H.-K., Sadler, P. J., & Sanchez-Cano, C. (2017). Synthesis and characterization of oxidovanadium complexes as enzyme inhibitors targeting dipeptidyl peptidase IV. Journal of Inorganic Biochemistry, 175, 29–35. https://doi.org/10.1016/j.jinorgbio.2017.06.014
   PubMed Web of Science ®Google Scholar
• Zaltariov, M. F., Hammerstad, M., Arabshahi, H. J., Jovanović, K., Richter, K. W., Cazacu, M., Shova, S., Balan, M., Andersen, N. H., Radulović, S., Reynisson, J., Andersson, K. K., & Arion, V. B. (2017). New iminodiacetate-thiosemicarbazone hybrids and their copper(II) complexes are potential ribonucleotide reductase R2 inhibitors with high antiproliferative activity. Inorganic Chemistry, 56(6), 3532–3549. https://doi.org/10.1021/acs.inorgchem.6b03178
   PubMed Web of Science ®Google Scholar